Ammonia → 4-Bromo-3,5-dimethoxybenzamide

Participants

Reaction Steps

To a mixture of 4-bromo-3,5-dimethoxybenzoic acid (15 g, 57.6 mmol) and THF (200 mL), were added triethylamine (9.63 mL, 69.0 mmol) and ethyl chloroformate (5.79 mL, 60.6 mmol) while stirring on ice, and the mixture was stirred on ice for 20 minutes. To the mixture, 28% aqueous ammonia was added and stirred at room temperature for two hours, followed by addition of ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The obtained residue (solid) was washed with diethyl ether, collected by filtration to obtain the title compound (11.8 g, 45.4 mmol).

Provenance & Evidence